Patent GB-727996-A (GB)
Title: Pigment dyestuffs of the anthraquinone series
IPC: C09B69/10
Filed: 1952-07-31
Abstract: Pigment dyestuffs are made by reacting an anthraquinone derivative of the formula <FORM:0727996/IV (c)/1> wherein R and R1 stand for organic radicals or hydrogen, at most one of the radicals R and R1 being hydrogen, and wherein the said radicals contain together at least two amino groups, with a polyfunctional compound capable of reacting with the external amino groups.  Polyfunctional compounds specified are aliphatic and aromatic diisocyanates, pyromellitic acid dianhydride, bis-ethylene oxide compounds, dicarboxylic phenyl esters, oxalic esters, diphenyl carbonate, methane-tricarboxylic esters, melamine-hexamethylol methylether, benzene disulphochloride, cyanuric chloride, terephthaloyl chloride, 1.3.5 - triacryloyl perhydro-s-triazine, and benzene disulpho-di-N.N1-ethylene imide. The reaction is preferably effected in a solvent such as chlorbenzene, nitrobenzene, or water at temperatures up to 200 DEG C.  In examples, (1) 1.4-bis-aminoethylamino-anthraquinone (obtained by mixing leuco - 1.4 - diamino - anthraquinone and excess ethylene diamine followed by oxidation) is heated in nitrobenzene with diphenyl carbonate to give a polyurea, or with oxalic acid dimethyl ester, or with terephthalic acid chloride in presence of pyridine; (2) 1.4-di-(p-aminohexahydrophenylamino) - anthraquinone (obtained by heating leuco-1.4-diaminoanthraquinone and excess hexahydro-p-phenylene diamine), 1.4 - bis - aminoethylaminoanthraquinone, or 1.4 - di - (p - aminophenylamino)-anthraquinone is heated in nitrobenzene with a mixture of 2.4- and 2.6-toluylene diisocyanate or in water with the bisulphite addition compound of hexamethylene diisocyanate; (3) 1.4 - di - (p - aminohexahydrophenylamino)-anthraquinone is reacted in dilute acetic acid with 1.3.5-triacryloylperhydro-s-triazine.  Other anthraquinone starting materials specified are those obtained by reacting quinizarin, leucoquinizarin, or leuco-1.4-diaminoanthraquinone with hexamethylene diamine, 1.2-diamino-3-hydroxypropane, hexahydrobenzidine, perhydronaphthalene diamines, N-methyl-1.3-propylene diamine, 3 - amino - 1 - a  - aminoethylbenzene, and o .o 1 - diaminodipropyl - diamino-butane.ALSO:Pigment dyestuffs are made by reacting an anthraquinone derivative of the formula <FORM:0727996/IV (a)/1> wherein R and R1 stand for organic radicals or hydrogen, at most one of the radicals R and R1 being hydrogen, and wherein the said radicals contain together at least two amino groups, with a polyfunctional compound capable of reacting with the external amino groups.  Polyfunctional compounds specified are aliphatic and aromatic diisocyanates, pyromellitic acid dianhydride, bis-ethylene oxide compounds, dicarboxylic phenyl esters, oxalic esters, diphenyl carbonate, methane-tricarboxylic esters, melamine-hexamethylol methyl-ether, benzene disulphochloride, cyanuric chloride, terephthaloyl chloride, 1,3,5-triacryloyl perhydro-s-triazine, and benzene disulpho di-N.N1-ethylene imide.  The reaction is preferably effected in a solvent such as chlorbenzene, nitrobenzene or water at temperatures up to 200 DEG  C.  In examples, (1) 1.4-diamino-anthraquinone and excess ethylene diamine followed by oxidation) is heated in nitrobenzene and diphenyl carbonate to give a polyurea, or with oxalic acid dimethyl ester, or with terephthalic acid chloride in presence of pyridine; (2) 1.4-di-(p-amino hexahydro - phenyl - amino) - anthraquinone (obtained by heating leuco-1.4-diaminoanthraquinone and excess hexahydro-p-phenylene diamine), 1.4 - bis - aminoethylaminoanthraquinone, or 1.4 - di - (p - aminophenylamino)-anthraquinone is heated in nitrobenzene with a mixture of 2.4- and 2.6-toluylene diisocyanate or in water with the bisulphite addition compound of hexamethylene diisocyanate; (3) 1.4-di-(p-aminohexahydrophenylamino)-anthraquinone is reacted in dilute acetic acid with 1,3,5-triacryloylperhydro-s-triazine. Other anthraquinone starting materials specified are those obtained by reacting quinizarin, leucoquinizarin, or leuco-1.4-diaminoanthraquinone with hexamethylene diamine, 1.2-diamino-3-hydroxypropane, hexahydro - benzidine, perhydronaphthalene diamines, N - methyl - 1.3 - propylene diamine, 3 - amino - 1 - aminoethyl - benzene, and w.w1-diaminodipropyl-diaminobutane.